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5'-O-(tert-butyldimethylsilyl)-3'-C-allyl-2',3'-dideoxythymidine | 120232-08-8

分子结构分类

有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷

中文名称

——

中文别名

——

英文名称

5'-O-(tert-butyldimethylsilyl)-3'-C-allyl-2',3'-dideoxythymidine

英文别名

1-[(2R,4S,5S)-4-allyl-5-[[tert-butyl(dimethyl)silyl]oxymethyl]tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione；1-[(2R,4S,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-prop-2-enyloxolan-2-yl]-5-methylpyrimidine-2,4-dione

5'-O-(tert-butyldimethylsilyl)-3'-C-allyl-2',3'-dideoxythymidine化学式

CAS

120232-08-8

化学式

C₁₉H₃₂N₂O₄Si

mdl

——

分子量

380.56

InChiKey

AJZMFWIZHTZCOB-ARFHVFGLSA-N

BEILSTEIN

——

EINECS

——

物化性质

熔点：

114-115 °C
密度：

1.049±0.06 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

3.35
重原子数：

26
可旋转键数：

7
环数：

2.0
sp3杂化的碳原子比例：

0.68
拓扑面积：

67.9
氢给体数：

1
氢受体数：

4

上下游信息

上游原料

中文名称	英文名称	CAS号	化学式	分子量
5’-O-(叔丁基二甲基甲硅烷基)胸苷	5'-tert-butyldimethylsilyloxy-2'-deoxythymidine	40733-28-6	C₁₆H₂₈N₂O₅Si	356.494
——	5'-O-<(1,1-Dimethylethyl)-dimethylsilyl>-3'-O-(phenoxythioxomethyl)thymidine	120232-06-6	C₂₃H₃₂N₂O₆SSi	492.668
beta-胸苷	thymidine	146183-25-7	C₁₀H₁₄N₂O₅	242.232

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	(E)-4-[(2S,3S,5R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-but-2-enoic acid methyl ester	202722-85-8	C₂₁H₃₄N₂O₆Si	438.596
——	1-[(2R,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(2-hydroxy-propyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione	202722-98-3	C₁₉H₃₄N₂O₅Si	398.575
——	1-[(2R,4R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(2-oxo-propyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione	202723-00-0	C₁₉H₃₂N₂O₅Si	396.559
——	3'-Propenyl-3'-deoxythymidine	120232-10-2	C₁₃H₁₈N₂O₄	266.297
——	1-[(2R,4S,5S)-4-Allyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-methyl-3-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrimidine-2,4-dione	202719-22-0	C₂₅H₄₆N₂O₅Si₂	510.822
——	1-[(2R,4S,5S)-4-Allyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-3-benzyloxymethyl-5-methyl-1H-pyrimidine-2,4-dione	202719-33-3	C₂₇H₄₀N₂O₅Si	500.711
——	{(2S,3R,5R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-[5-methyl-2,4-dioxo-3-(2-trimethylsilanyl-ethoxymethyl)-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-3-yl}-acetaldehyde	202719-23-1	C₂₄H₄₄N₂O₆Si₂	512.794
——	3'-Deoxy-3'-(2-propynyl)thymidine	128119-36-8	C₁₃H₁₆N₂O₄	264.281
——	3'-Cyanomethyl-3'-deoxythymidine	128119-37-9	C₁₂H₁₅N₃O₄	265.269
——	{(2S,3R,5R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-[5-methyl-2,4-dioxo-3-(2-trimethylsilanyl-ethoxymethyl)-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-3-yl}-acetic acid	202719-25-3	C₂₄H₄₄N₂O₇Si₂	528.794
——	[(2S,3R,5R)-5-(3-Benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl]-acetaldehyde	202719-34-4	C₂₆H₃₈N₂O₆Si	502.683
——	[(2S,3R,5R)-5-(3-Benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl]-acetic acid	202719-35-5	C₂₆H₃₈N₂O₇Si	518.682
——	1-[(2R,4R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(2-imidazol-1-yl-2-oxo-ethyl)-tetrahydro-furan-2-yl]-5-methyl-3-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrimidine-2,4-dione	202724-76-3	C₂₇H₄₆N₄O₆Si₂	578.856
——	3-Benzyloxymethyl-1-[(2R,4R,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-(2-imidazol-1-yl-2-oxo-ethyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione	202724-78-5	C₂₉H₄₀N₄O₆Si	568.745
——	1-[(2R,4S,5S)-4-Allyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-3-(4-methoxy-benzyl)-5-methyl-1H-pyrimidine-2,4-dione	151294-47-2	C₂₇H₄₀N₂O₅Si	500.711
——	1-[(2R,4R,5S)-5-Aminomethyl-4-(2,2-dimethoxy-ethyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione	403999-94-0	C₁₄H₂₃N₃O₅	313.354
——	[(2S,3R,5R)-2-Aminomethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetaldehyde	403999-95-1	C₁₂H₁₇N₃O₄	267.285
——	{(2S,3R,5R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-[3-(4-methoxy-benzyl)-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-3-yl}-acetaldehyde	151294-48-3	C₂₆H₃₈N₂O₆Si	502.683
——	{(2S,3R,5R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-[3-(4-methoxy-benzyl)-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-3-yl}-acetic acid	151294-49-4	C₂₆H₃₈N₂O₇Si	518.682
——	1-{(2R,4R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-[2-oxo-3-(triphenyl-λ⁵-phosphanylidene)-propyl]-tetrahydro-furan-2-yl}-5-methyl-3-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrimidine-2,4-dione	202719-28-6	C₄₃H₅₉N₂O₆PSi₂	787.096
——	1-[(2R,4R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(2-imidazol-1-yl-2-oxo-ethyl)-tetrahydro-furan-2-yl]-3-(4-methoxy-benzyl)-5-methyl-1H-pyrimidine-2,4-dione	151294-50-7	C₂₉H₄₀N₄O₆Si	568.745
——	3-Benzyloxymethyl-1-{(2R,4R,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-[2-oxo-3-(triphenyl-λ⁵-phosphanylidene)-propyl]-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione	202719-37-7	C₄₅H₅₃N₂O₆PSi	776.985
——	1-{(2R,4R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-[2-oxo-3-(triphenyl-λ⁵-phosphanylidene)-propyl]-tetrahydro-furan-2-yl}-3-(4-methoxy-benzyl)-5-methyl-1H-pyrimidine-2,4-dione	151294-51-8	C₄₅H₅₃N₂O₆PSi	776.985
——	[(2S,3R,5R)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetaldehyde	403999-90-6	C₂₀H₁₉N₃O₆	397.387
——	[(2S,3R,5R)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetic acid	404000-31-3	C₂₀H₁₉N₃O₇	413.387

反应信息

作为反应物：

描述：

5'-O-(tert-butyldimethylsilyl)-3'-C-allyl-2',3'-dideoxythymidine 在 sodium periodate 、四氧化锇、羟胺、 N,N'-羰基二咪唑作用下，生成 1-[5-O-(tert-butyldimethylsilyl)-3-C-(2-cyanoethyl)-2,3-dideoxy-β-D-erythro-pentofuranosyl]thymine

参考文献：

名称：

AZT类似物3'-脱氧-3'-（2-丙炔基）胸苷和3'-氰甲基-3'-脱氧胸苷的合成

摘要：

描述了一种使用自由基化学方法将碳取代基引入3'-脱氧胸苷3'-位的有效方法。提出了该方法在AZT的两个紧密类似物3'-脱氧-3'-（2-丙炔基）胸苷和3'-氰甲基-3'-脱氧胸苷的合成中的应用。

DOI：

10.1016/s0040-4039(00)94577-5
作为产物：

描述：

5’-O-(叔丁基二甲基甲硅烷基)胸苷在 4-二甲氨基吡啶作用下，以二氯甲烷、甲苯为溶剂，生成 5'-O-(tert-butyldimethylsilyl)-3'-C-allyl-2',3'-dideoxythymidine

参考文献：

名称：

AZT类似物3'-脱氧-3'-（2-丙炔基）胸苷和3'-氰甲基-3'-脱氧胸苷的合成

摘要：

描述了一种使用自由基化学方法将碳取代基引入3'-脱氧胸苷3'-位的有效方法。提出了该方法在AZT的两个紧密类似物3'-脱氧-3'-（2-丙炔基）胸苷和3'-氰甲基-3'-脱氧胸苷的合成中的应用。

DOI：

10.1016/s0040-4039(00)94577-5

点击查看最新优质反应信息

文献信息

Mellor, Ben J.; Thomas, Eric J., Journal of the Chemical Society. Perkin transactions I, 1998, # 4, p. 747 - 757

作者：Mellor, Ben J.、Thomas, Eric J.

DOI：——

日期：——
Modified ollgonucleotides. Effect of 4 vs 5-atom chimeric internucleoside linkages on duplex stability

作者：Gilbert Stork、Chengzhi Zhang、Sergel Gryaznov、Ronald Schultz

DOI：10.1016/0040-4039(95)01320-h

日期：1995.9

The question whether a four or a five atom non phosphorus based internucleoside link leads to stronger binding of the resulting chimeric oligonucleotides to complementary sequences has been examined by comparing melting temperatures of relevant duplexes.
DNA-Catalyzed Polymerization

作者：Xiaoyu Li、Zheng-Yun J. Zhan、Rachel Knipe、David G. Lynn

DOI：10.1021/ja017319j

日期：2002.2.1

Native DNA oligomers are shown to be stereoselective catalysts for the polymerization of 5'-amino-3'-acetaldehyde-modified thymidine/adenosine nucleosides through reductive amination. The reaction follows step-growth kinetics to read the encoded sequence and chain-length information in the antiparallel direction. Single mismatches in the template are selected against at a level of >100:1. A method is therefore established to translate biopolymer-encoded information stereoselectively into sequence- and chain-length specific synthetic polymers.
Polymerization on Solid Supports

作者：Xiaoyu Li、David G. Lynn

DOI：10.1002/1521-3773(20021202)41:23<4567::aid-anie4567>3.0.co;2-6

日期：2002.12.2
Kawai, Stephen H.; Wang, Daguang; Just, George, Canadian Journal of Chemistry, 1992, vol. 70, # 5, p. 1573 - 1580

作者：Kawai, Stephen H.、Wang, Daguang、Just, George

DOI：——

日期：——